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Enantioselective Synthesis of α-N-Alkylamino Acids via Sultam-Directed "Enolate" Hydroxyamination

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Oppolzer, Wolfgang
Cardinaux, Francis
Published in Helvetica Chimica Acta. 1993, vol. 76, no. 1, p. 187-196
Abstract Crystalline N-hydroxyamino-acid derivatives 4, readily available from non-chiral acyl chlorides 2 and sultams 1, were treated with aldehydes in the presence of NaBH3CN to give N-alkylhydroxylamines 5. N,O-Hydrogenolysis of 5 and saponification of 6 furnished (S)-N-alkylamino acids 7 in high optical purity. Similarly, (R)-N-alkylamino acids 12 were obtained from the antipodal acylsultams 8.
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Other version: http://doi.wiley.com/10.1002/hlca.19930760113
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OPPOLZER, Wolfgang et al. Enantioselective Synthesis of α-N-Alkylamino Acids via Sultam-Directed "Enolate" Hydroxyamination. In: Helvetica Chimica Acta, 1993, vol. 76, n° 1, p. 187-196. https://archive-ouverte.unige.ch/unige:86082

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